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Methyl phenylacetate → Benzeneacetic acid, alpha-bromo-, methyl ester

HRID 3973
Notes
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Reaction equation

HRID 3973 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:16]([O:18][CH3:19])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7559Methyl phenylacetateHCID 67184N-bromobutanimide

Product 1

HCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterYield 93.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

In this example, a mixture containing 5.93 g of N-bromosuccinimide, 5.0 g of methyl phenylacetate; and a catalytic amount (about 0.1 g) of benzoyl peroxide in 50 ml of carbon tetrachloride was warmed to reflux and then refluxed for about 12 hours. The mixture was then cooled to about 0° C. and filtered. The filtrate was concentrated by evaporation under vacuum affording 7.1 g of the title compound as an oil.

Workup

  1. temperatureto reflux
  2. temperaturerefluxed for about 12 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated by evaporation under vacuum

Sources & evidence

ORD record
ord-5dcd18cf32f744b38e1a3a9e2e554156
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04723031

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes